3310. Diphenic Acid

Nomenclature

CAS number: 482-05-3
[1,1′-Biphenyl]-2,2′-dicarboxylic acid; o,o′-bibenzoic acid.
C14H10O4; mol wt 242.23.
C 69.42%, H 4.16%, O 26.42%.

Description and references

Prepd from diazotized anthranilic acid by treatment with a cuproammonia-sulfite reducing agent: Vorl"ander, Meyer, Ann. 320, 122 (1902); Atkinson, Lawler, Org. Synth. coll. vol. I (2nd ed, 1941) p 222. By chromic acid oxidation of phenanthrenequinone: Roberts, Johnson, J. Am. Chem. Soc. 47, 1399 (1925). By heating potassium o-bromobenzoate with copper powder: Hurtley, J. Chem. Soc. 1929, 1870.

Chemical structure

Properties

Monoclinic prismatic rods upon slow cooling from water, leaflets from hot water, needles by careful sublimation. mp 228-229°. The satd aq soln is 0.0052N at 25°; soluble in the usual organic solvents.

Derivative

Dimethyl ester.
C16H14O4; mol wt 270.28.
C 71.10%, H 5.22%, O 23.68%.

Properties

Monoclinic prismatic plates, tablets from methanol, mp 73.5°; bp14 204-206°.

Derivative

Diethyl ester.
C18H18O4; mol wt 298.33.
C 72.47%, H 6.08%, O 21.45%.

Properties

Cubes from alcoholic HCl, mp 42°.